Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (7): 2693-2699.DOI: 10.6023/cjoc202102048 Previous Articles Next Articles
收稿日期:
2021-02-26
修回日期:
2021-04-02
发布日期:
2021-06-07
通讯作者:
王雪
基金资助:
Received:
2021-02-26
Revised:
2021-04-02
Published:
2021-06-07
Contact:
Xue Wang
Supported by:
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Xue Wang. Reduction of Trifluoromethyl Ketones with Diethyl Zinc Catalyzed by Chiral Monophosphoryl Protected Diamine[J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2693-2699.
Entry | Ligand | X | R1 | R2 | Yield/% | eeb/% | Config.c |
---|---|---|---|---|---|---|---|
1 | 10[ | — | — | — | 77 | 48 | R |
2 | 11a[ | O | — | — | 20 | 12 | S |
3 | 11b[ | S | — | — | 19 | 11 | S |
4 | 9a | O | Bn | Bn | 96 | 55 | R |
5 | 9b[ | S | Bn | Bn | 93 | 48 | R |
6 | 9c[ | O | Et | H | 75 | 8 | R |
7 | 9d[ | O | i-Pr | H | 88 | 19 | S |
Entry | Ligand | X | R1 | R2 | Yield/% | eeb/% | Config.c |
---|---|---|---|---|---|---|---|
1 | 10[ | — | — | — | 77 | 48 | R |
2 | 11a[ | O | — | — | 20 | 12 | S |
3 | 11b[ | S | — | — | 19 | 11 | S |
4 | 9a | O | Bn | Bn | 96 | 55 | R |
5 | 9b[ | S | Bn | Bn | 93 | 48 | R |
6 | 9c[ | O | Et | H | 75 | 8 | R |
7 | 9d[ | O | i-Pr | H | 88 | 19 | S |
Entry | Y | Z | Solvent | Temp./℃ | Time/h | Yeildb/% | eec/% |
---|---|---|---|---|---|---|---|
1 | 0.8 | 20 | Hexane | 0 | 5 | 31 | 22 |
2 | 1.5 | 20 | Hexane | 0 | 5 | 90 | 53 |
3 | 2.0 | 20 | Hexane | 0 | 5 | 93 | 51 |
4 | 3.0 | 20 | Hexane | 0 | 5 | 97 | 28 |
5 | 2.0 | 30 | Hexane | 0 | 5 | 89 | 54 |
6 | 2.0 | 20 | CH2Cl2 | 0 | 5 | 84 | 55 |
7 | 2.0 | 20 | Toluene | 0 | 5 | 95 | 54 |
8 | 2.0 | 20 | Toluene | 0 | 12 | 96 | 63 |
9 | 2.0 | 20 | Toluene | 0 | 24 | 94 | 77 |
10 | 2.0 | 20 | Toluene | –10 | 24 | 92 | 80 |
11 | 2.0 | 20 | Toluene | –20 | 24 | 91 | 88 |
Entry | Y | Z | Solvent | Temp./℃ | Time/h | Yeildb/% | eec/% |
---|---|---|---|---|---|---|---|
1 | 0.8 | 20 | Hexane | 0 | 5 | 31 | 22 |
2 | 1.5 | 20 | Hexane | 0 | 5 | 90 | 53 |
3 | 2.0 | 20 | Hexane | 0 | 5 | 93 | 51 |
4 | 3.0 | 20 | Hexane | 0 | 5 | 97 | 28 |
5 | 2.0 | 30 | Hexane | 0 | 5 | 89 | 54 |
6 | 2.0 | 20 | CH2Cl2 | 0 | 5 | 84 | 55 |
7 | 2.0 | 20 | Toluene | 0 | 5 | 95 | 54 |
8 | 2.0 | 20 | Toluene | 0 | 12 | 96 | 63 |
9 | 2.0 | 20 | Toluene | 0 | 24 | 94 | 77 |
10 | 2.0 | 20 | Toluene | –10 | 24 | 92 | 80 |
11 | 2.0 | 20 | Toluene | –20 | 24 | 91 | 88 |
Entry | Product | 12 (Config.) | Yielda/% | eeb/% |
---|---|---|---|---|
1 | | 12a (R) | 91 | 88 |
2 | | 12b (R) | 77 | 60 |
3 | | 12c (R) | 73 | 63 |
4 | | 12d (R) | 71 | 66 |
5 | | 12e (R) | 76 | 67 |
6 | | 12f (R) | 90 | 53 |
7 | | 12g (R) | 91 | 76 |
8 | | 12h (R) | 89 | 73 |
9 | | 12i (R) | 85 | 91 |
10 | | 12j (R) | 81 | 78 |
11 | | 12k (S) | 76 | 87 |
12 | | 12l (S) | 85 | 62 |
Entry | Product | 12 (Config.) | Yielda/% | eeb/% |
---|---|---|---|---|
1 | | 12a (R) | 91 | 88 |
2 | | 12b (R) | 77 | 60 |
3 | | 12c (R) | 73 | 63 |
4 | | 12d (R) | 71 | 66 |
5 | | 12e (R) | 76 | 67 |
6 | | 12f (R) | 90 | 53 |
7 | | 12g (R) | 91 | 76 |
8 | | 12h (R) | 89 | 73 |
9 | | 12i (R) | 85 | 91 |
10 | | 12j (R) | 81 | 78 |
11 | | 12k (S) | 76 | 87 |
12 | | 12l (S) | 85 | 62 |
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